An adamantanol derivative compound is a useful material as an commercial material. Specifically, a ketone among the adamantanol derivative compound is chemically used with comparative ease as a novel material or a material for medicines or agricultural chemicals, and commercial values thereof are increasing.
As a laboratory-level process for producing adamantanone, some technical examples using a three-step reaction are reported. The reaction comprises cationizing a separately prepared tertiary adamantanol, generating a secondary adamantanol with maintaining an equilibrium via 1,2-sigmatropy and converting it to an irreversible ketone body in a further continuous oxidation.
Schlatmann, for example, has reported that 2-adamantanone can be obtained in 72% yield by heating to maintain 1-adamantanol in concentrated sulfuric acid for 12 hours at 30.degree. C. [Tetrahedronn, 24, 5361 (1968)].
Further, Geluk has reported that 2-adamantanol can be obtained in 50% yield from adamantane and in 70% yield from 1-damantanol, respectively, by heating to maintain them in 120-fold eqiv. concentrated sulfuric acid for 5 hours at 70.degree. C. [Tetrahedronn, 24, 5369 (1968)].
These producing process, however, is not commercially suitable process because of using a large quantity of concentrated sulfuric acid. Moreover, the reaction is conducted under severe condition. Further, it is reported in these literatures that a slight deterioration of the condition of super strong acid insures a decrease of the yield of the ketone body, thus controlling the acidic condition is highly difficult. On the other hand, any process for producing a commercially useful hydroxyketone, polyketone or the like has not been reported.
Incidentally, a compound substituted by a hydroxyl group at a tertiary carbon atom of the site connecting adjacent rings each other, is useful as a physiologically active substance and has high utility values as an antiviral drug (agent), an antibacterial drug (agent), a plant hormone, and so forth. A compound bound by a functional group at a carbon atom of the connecting site of the rings, is broadly utilized as a raw material of various perfumes, a fragrant compound. Thus, a tertiary alcohol body having a hydroxyl group at the connecting site of rings, is an important compound. Therefore, producing a hydroxyketone body, which is a tertiary alcohol body and ketone body having a hydroxyl group at the connecting site of rings, is exceedingly important.
Japanese Patent Application Laid-open No. 38909/1996 (JP-A-8-38909) proposes a process for generating adipic acid by oxidizing cyclohexanone or cyclohexanol with molecular oxygen in the presence of an oxidation catalyst comprising an imide compound. A process for generating isocoumarin by oxidizing isochroman with molecular oxygen in the presence of the oxidation catalyst comprising the imide compound is also proposed.
On the page 762 of the "Lecture Draft II" (1994) of 67th Spring Annual Meeting of Chemical Society of Japan, it is reported that oxidation of adamantane with oxygen by using N-hydroxyphthalimide provides a corresponding alcohol or ketone. However, producing a ketone body or a hydroxyketone body, effectively and efficiently, with controlling a generation of a polyol body of a polycyclic hydrocarbon such as adamantane, is difficult. Specifically, it is difficult to give the ketone body and the hydroxyketone body with high conversion and selectivity.